Aluminium lithium hydride → HCID 21964299, compound

HRID 2373495Notes

Reaction equation

[C:1]([C:5]1[CH:27]=[CH:26][C:8]([CH2:9][N:10]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=3)[CH:12]=[C:11]2[C:21](OCC)=[O:22])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[C:1]([C:5]1[CH:27]=[CH:26][C:8]([CH2:9][N:10]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=3)[CH:12]=[C:11]2[CH2:21][OH:22])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 21226445Aluminium lithium hydride

HCID 21964306HCID 21964306, compound

Product 1

HCID 21964299HCID 21964299, compound

Procedure

The title compound was prepared from ethyl 1-(4-tert-butylbenzyl)-5-methoxy-1H-indole-2-carboxylate and lithium aluminum hydride in substantially the same manner, as described in step 3 of Example 1. The product was obtained as an oil. Mass spectrum (ESI, [M−H]−) m/z 322. 1H NMR (400 MHz, DMSO-d6) δ 7.27 (d, 2H, J=8.14 Hz), 7.20 (d, 1H, J=8.70 Hz), 7.01 (d, 1H, J=2.45 Hz), 6.94 (d, 2H, J=8.24 Hz), 6.68 (dd, 1H, J=8.85 and 2.44 Hz), 6.34 (s, 1H), 5.37 (s, 2H), 5.26 (t, 1H), 4.56 (d, 2H, J=4.43 Hz), 3.72 (s, 3H), and 1.21 ppm (s, 9H).

Workup

customThe product was obtained as an oil

Sources & evidence

ORD record: ord-0f3c4aec7b0345d39181a65ed222aef6
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459478B2

Reaction notes

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